It’s an auction like no other. On 5 December, the international auction house Phillips is set to host Styled, an auction of 121 collectors’ watches split into 12 different themes, each corresponding to a moment in a modern gentleman’s life.

Working in collaboration with Phillips are MR PORTER and The Rake, who have each designed a series of outfits to correspond with the themes. The outfits, which were designed for occasions such as a man’s wedding day or a Caribbean summer vacation, will be on show as a series of interactive vignettes at the Phillips headquarters in New York from 30 November until the evening of the auction. If you can’t make it to New York, though, don’t worry, as we’ve collected all of MR PORTER’s outfits – and the incredible watches they’re designed to be worn with – right here.

“A wrist watch so accurate you only set it once a year.” That was the advertising slogan announcing the 1969 release of Patek Philippe’s Beta 21. It sounds like a bold claim for a mechanical watch, and it is. But the Beta 21, you see, isn’t a mechanical watch. Featuring a quartz movement developed by the Centre Electronique Horloger (CEH), a research group founded in 1962 by a consortium of Swiss watch brands that included Patek Philippe, Rolex, Omega and Piaget, the Beta 21 was Patek’s rearguard action against the onslaught of Japanese quartz technology. It’s a piece of horological history, a real conversation starter and a beautiful watch to boot. This particular example, a ref. 3587/1 from 1971 in 18-karat white gold, is being offered at auction with an estimate of $25,000 to $35,000.

With its bold dimensions – at 43mm, this is the largest serially produced wristwatch ever made by Patek Philippe – and its decidedly post-modern looks, the Beta 21 is a smart choice for Phillips’ art fair category, which was conceived with Art Basel Miami Beach in mind. We’ve completed the look with a softly tailored, herringbone-wool suit from Berluti and grown-up sneakers from Brunello Cucinelli.

Cartier’s Tank Américaine was originally introduced in 1989 as a larger, more masculine update to the classic Tank Cintrée, which was regarded as a touch effeminate in the testosterone-heavy late 1980s. A curved, elongated rectangle with sharply defined edges that complement a well-pressed double cuff on a dress shirt, the Tank Americaine is an obvious choice for Phillips’ evening-wear category. The model in this picture dates from around 1998 and is in excellent condition, its 45mm platinum case still bearing the original factory finish. If you’re hoping to pick it up at auction, expect to pay between $6,000 and $8,000.

Now that you’ve raised the stakes with a dress watch as elegant as this, you’ll need a tuxedo to match. This one is made by Tom Ford and features generous satin lapels and turn-back cuffs. It’s worn here with chain-trimmed velvet loafers from the same brand, while the bib-front tuxedo shirt is made by the ultra-minimal Dutch brand Salle Privée.

Glorious Goodwood deserves an equally glorious watch, and this military-issue Omega Seamaster 300 fits the brief perfectly. Introduced in 1957 as part of Omega’s Professional line alongside the now-iconic Speedmaster, the Seamaster 300 was one of the Swiss brand’s first forays into the subaquatic world of diving watches. It has since become one of its most popular lines and since 1995 has been the watch of choice for James Bond. This incredibly rare and well-preserved example, which was made in 1967 for the British Royal Army’s elite Special Air Service (SAS) division, is going to auction in December with an estimate of between $50,000 and $100,000.

The Omega isn’t the only thing in this picture boasting rugged vintage looks and serious military pedigree. We’ve paired it with a sturdy, shearling-lined bomber jacket from Brunello Cucinelli, which takes its design cues from the G-1 bomber jackets worn by the US military in the 1940s, a burgundy rollneck sweater from Dunhill and a pair of wool-flannel cargo trousers, also from Brunello Cucinelli. The finishing touch? A pair of suede Gommino driving shoes from Tod’s.

Jaeger-LeCoultre’s reference E859 “Memovox Polaris” was first introduced in 1968 as a diving watch with a mechanical alarm, the idea being that you could programme the alarm to “ping” when it was time to return to the surface. Only 1,714 examples of this strange, yet highly influential watch were ever made, and with JLC having recently reintroduced the Polaris to its modern lineup, there’s no better time than now to get your hands on one of the originals. This particularly well-preserved example from 1968 has an auction reserve of $12,000 to $14,000.

Adverts of the era proclaimed the Polaris as a watch “pour l’homme d’action” or “for the man of action”, and while it was primarily intended as a diving instrument, Jaeger-LeCoultre’s definition of “action” is surely a little broader and more inclusive than just that. We think it’s just as suitable for land-based adventures, and Phillips seem to agree, giving it pride of place in their “safari” category. We’ve anchored the coordinating look with a cotton-canvas field jacket from Aspesi, which is modelled on military-issue M65s, but bears more than a passing resemblance to safari jackets of colonial times. It’s set off with a waffle-knit Henley shirt from RRL, a pair of herringbone stretch-cotton cargo trousers, burnished hiking boots from Tom Ford and a suede rucksack from Brunello Cucinelli.

Designed in 1976 by the legendary Mr Gérald Genta, the man responsible for Audemars Piguet’s Royal Oak, the Nautilus was Patek Philippe’s first foray into the sports-luxury market. Nautical by name and by nature, it was styled “Nautilus” after Captain Nemo’s submarine in Mr Jules Verne’s Twenty Thousand Leagues Under The Sea, while those distinctive “ears” were designed to resemble the hinges of a submarine’s porthole. A groundbreaking watch from Switzerland’s preeminent watchmaker, it remains one of the most sought after watches in production today, making this early model – an original ref. 3700/1 from 1980 – a high-profile lot and fully deserving of its $50,000 to $100,000 estimate.

And so to the question of how, and indeed where, to best wear a Nautilus. You’d think a regatta would be a smart choice, given the watch’s distinctive marine feel, and while it certainly wouldn’t look out of place on a skipper’s wrist, Phillips suggests that you take it on your next trip to Aspen, Nozawa Onsen or Courchevel instead. We’ve designed an après-ski outfit to match, featuring a zipped cardigan from Brunello Cucinelli, a rollneck sweater from Canali, fine-waled corduroy trousers from Loro Piana and a pair of waterproof boots from Sorel. All you need is a glass of gluhwein and you’re away.

This rare edition of Rolex’s classic Day-Date is one of the stars of Phillips’ auction category dedicated to the Caribbean, and if you’re wondering why, just look at that gorgeous, sea-green dial. The material in question is malachite, a copper crystal known for its swirling bands of vibrant colour that can be seen here playing beautifully against the 18-karat yellow gold of the case and bracelet. The rarity and fine condition of this watch – plus the fact that it’s a Rolex – are reflected in an estimated price of between $20,000 and $40,000.

We’ve paired this eye-catching timepiece with an attention-grabbing bowling shirt from Prada, an exclusive from our retro-themed capsule with the Italian brand. Completing the look are a pair of pleated wide-leg trousers from Gucci, which are cinched in at the waist by a belt from Dries Van Noten, a pair of leather slides from Álvaro and some pink-tinted shades from Berluti. Very Mr Hunter S Thompson, as we’re sure you’ll agree.

If you ever find yourself wondering which watch to wear on your summer trip to Positano, then congratulations – you’ve made it. On a more practical note, might we suggest a vintage Heuer Mareographe? This peculiar chronograph with built-in tidal indicator began life in the 1940s as the Solunar, a time-only watch designed by Mr Jack Heuer with help from his high-school physics teacher. By the early 1960s, it had evolved to the form seen here, the blue-accented dials at nine and three o’clock instantly marking it out to in-the-know collectors. With an unpolished case and well-preserved dial, this particular example is sure to pique the interest of vintage Heuer lovers when it goes to auction with an estimate of $4,000 to $6,000.

The outfit we’ve chosen to go with this watch is light on blue, a sensible decision given the blue accents on the watch face, and, of course, the famously blue waters you’ll be surrounded by in Positano. Instead, we’ve opted for a simple, layered look comprised of a lightweight linen shirt from Sydney tailor P. Johnson, a burgundy cardigan from Boglioli that blurs the lines between sweater and unstructured jacket, and a pair of pleated shorts from the masters of Neapolitan elegance, Rubinacci. Note, too, the suede espadrilles in Bottega Veneta’s house Intrecciato weave, the beaded bracelet from the Japanese jeweller Mikia and the tan tote bag from Dunhill. This is an ensemble that’s all about the finishing touches.

The unapologetically masculine Royal Oak “Offshore” from Audemars Piguet was one of the catalysts for the big watch trend of the late 1990s and early 2000s, paving the way for brands such as Hublot and Roger Dubuis and introducing a new generation to the world of high-end Swiss horology. A steroidally enhanced take on Mr Gerald Genta’s original Royal Oak, the Offshore carries over the octagonal, diver’s helmet-inspired design but adds more – more weight, more girth, more everything. A controversial watch when it was first unveiled in 1993, it’s now coming to be seen as something of a modern classic, which goes to show how ahead of its time it was. The watch in question here, a perpetual calendar with moon phase indicator from 2007, is estimated at $20,000 to $30,000.

With its 42mm diameter and muscular, exaggerated proportions, the Royal Oak Offshore is a sports watch through and through, and unlike its predecessor, it’s not one that could easily double up as a business watch – unless you happen to work on a yacht. With this in mind, Phillips has placed it in its Hamptons category, and we’ve provided a simple, summer-ready outfit to go along with it. At its heart is a chunky cardigan from RRL emblazoned with an eagle intarsia, a pair of cotton-twill drawstring shorts from Hartford, boat shoes from the Los Angeles artisanal shoemaker Yuketen and a pair of retro-inspired tortoiseshell sunglasses from Kirk Originals.

It was Mr Louis-Abraham Breguet who first invented the tourbillon regulator, a rotating cage designed to minimise the effects of gravity on a watch’s escapement, so it’s fitting that a tourbillon watch such as this should also bear his name. The tourbillon is prized not only for its technical innovation but also for how beautiful it looks, and there’s no better way of viewing one in all its glory than in a skeletonized case, in which the bridges and plates holding the watch together have been carved away to reveal its bare bones and beating heart. If you’re interested in what goes on “under the hood”, as it were, then this is one watch that’s sure to catch your eye. It’ll be available at auction this December with an estimate of $30,000 to $50,000.

Sensibly concluding that this is a watch best reserved for special occasions, Phillips chose to nominate Breguet’s skeletonised tourbillon for its “wedding” category. Is there a more special occasion, after all, than the day of your nuptials? As to the question of what to wear, MR PORTER has opted for city wedding-appropriate attire comprised of a light blue suit from Dunhill, a striped knitted tie from Canali and a pair of full-grain penny loafers from George Cleverley. Completing the look are a printed wool- and yak-blend pocket square from Anderson & Sheppard and a pair of D-frame tortoiseshell acetate sunglasses from Brioni.

Even contemporary examples of Rolex’s iconic GMT-Master are highly sought after collectors’ items, so it’s no surprise that this beautifully preserved, 60-year-old version – an original reference 6542 in 18-karat yellow gold with luminous Bakelite bezel – is considered one of the highlights of Phillips’ upcoming auction. The estimate is set at $100,000 to $200,000; expect bidding to be fierce.

Assuming you win it, how would you wear it? As expected of a watch bearing the iconic Rolex crown, this GMT-Master manages the trick of being both sporty and smart – so why not take it to Wimbledon? There are few occasions in the sporting calendar quite as dapper as the All England Lawn Tennis and Croquet Club’s annual Grand Slam, a tournament that as recently as 2014 still advised Court One and Centre Court debenture holders to avoid jeans and collarless shirts. Accordingly, we’ve incorporated this Rolex into a smart ensemble consisting of a navy double-breasted blazer, stone chinos and a chambray shirt, accessorised with a polka-dot tie from Drake’s, a pin-dot pocket square from Anderson & Sheppard and, of course, an umbrella. A pair of whole-cut Oxfords from Berluti complete a look worthy of the Royal Box.

The “Chronomètre à Résonance” is one of Mr Francois Paul Journe’s most ingenious inventions. Introduced in 2000, it features two movements whose balance wheels oscillate in harmony with one another, theoretically stabilising any variations that might occur due to movement of the wrist. Placing this technology in a wristwatch is an achievement that eluded many of history’s greatest watchmakers, including none other than Mr Abraham-Louis Breguet. The perfect watch for high achievers, then, and all the better when rendered in 18-karat pink gold, as in the case of this particular example, which will be going to auction this December with an estimate of $20,000 to $30,000.

Horological wizardry aside, why would you want it? Well, how about the fact that it also makes for an excellent business watch? Not only does it boast impeccable looks, but it also has a dual-time function that’s sure to come in handy for anyone used to working across two time zones. Little wonder, then, that the experts at Phillips chose it for their business category. We’ve paired it with a double-breasted pinstripe suit from our very own Kingsman collection, a tie and shirt from Charvet, monk-strap shoes from Edward Green and a beautifully burnished, supple leather briefcase from Berluti. Consider this power dressing done properly.

This 38.5mm stainless-steel chronograph from Vacheron Constantin is known as “Cornes de Vache”, meaning “bull’s horns”, a reference to the extravagantly curved teardrop lugs. Released in February 2017 as a limited edition of 36 pieces and retailed exclusively via the online watch magazine HODINKEE, it sent shockwaves through the watch world – a latecomer to the ecommerce revolution – by selling out in less than half an hour. This particular model goes to auction on 5 December with an estimate of $20,000 to $30,000.

A much-hyped timepiece that caused a great deal of noise in the watch industry, Vacheron Constantin’s Cornes de Vache is the perfect choice for a gathering of watch enthusiasts, say the experts at Phillips. But, while there are few moments in a man’s life when he is likely to find his wrist under greater scrutiny, that doesn’t mean that he should neglect the rest of his outfit. We approached this look knowing that at events like these, dress codes tend to be unwritten, giving the attendee freedom to express himself how he pleases. This ensemble – a medley of cream, caramel and oatmeal shades, topped off by a beautiful chocolate suede jacket from Berluti – says all the right things.

See it for yourself: these outfits will be on show at the Phillips headquarters in New York from 30 November until 5 December